


Girls Just Want To Have Fun

by FPwoper



Series: 31 days of... ships [9]
Category: Supernatural
Genre: Discussion of explicit sex, F/M, MTF Castiel, Pegging, Sex Toys, Trans Character, no explicit dean/cas
Language: English
Status: Completed
Published: 2019-10-14
Updated: 2019-10-14
Packaged: 2020-12-15 22:22:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,509
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21025676
Author URL: https://archiveofourown.org/users/FPwoper/pseuds/FPwoper
Summary: Charlie and Castiel are goofing off, drunk, when Charlie asks Cas: "Have you ever pegged anyone?"Prompts (day 13):Suptober: LadiesKinktober: Pegging





	Girls Just Want To Have Fun

**Author's Note:**

> Thank you so much to thunderthighsmish (on AO3) and farkenshnoffingottom (also on AO3) for being my amazing sensitivity readers.  
This short thing turned out to be something very emotional, and I have to say that this is probably my favourite so far.

“Have you ever pegged anyone?” Charlie asks. It’s late at night, and both her and Cas are drunk as fuck. Cas giggles and flushes.

“Dean… Dean has such a weird thing about his ass,” she finally manages. “He loves it when I play with his ass, like… fingering and prostate massages are all fine, but as soon as I want to grab one of my dildos, he suddenly has something else to do.”

Charlie almost chokes on her beer before breaking out in great guffaws. “That’s both too much information and also not quite enough. How the fuck did you get the great macho Dean to even take a fucking _finger _up his ass?”

“Quite by accident,” Cas says. She’s now hanging on the couch upside down, head almost on the rug on the floor. “We were just sort of… playing around, and I might have been sucking him off…” Cas flushes and looks at Charlie. “Are you sure you want all these details? I’m probably going to get more graphic the more we drink.”

“I love it,” Charlie says, cheeks almost as red as her hair. “It’s definitely going to be blackmail material for the future, just so you know.”

Castiel laughs again – evenings with just Charlie always make her feel so free. She hasn’t always been open about her sexuality and the fact that she struggled with her gender identity, but Charlie makes her feel at home. And Charlie doesn’t judge her for being in a relationship with Dean, which initially looked like it wasn’t going to work out. The number of times Cas had sat in Charlie’s living room, crying because Dean didn’t understand why Cas was having a bad day… Cas shakes her head. “Good to know. I’ll also tell you about the worst things about Dean, okay? Just remind me to do that.” She falls quiet for a little bit, and then remembers where she was. “Oh yeah, so – I was sucking Dean off, and sort of figuring out where the fuck I should be putting my hands. It’s awkward to not hold onto his hips but also I was getting bored with that, so I started playing with his balls and slowly slipping further and I think Dean wasn’t really paying attention because I just… brushed over his hole and he immediately blew his load.”

“Wait, just like that?” Charlie asks, sounding incredulous. “I know there’s this… super sensitive place but… really?”

Castiel nods. “I honestly don’t know if it was because he was on the verge of coming or whether it was because I touched his hole but sure, yeah. After that it sort of just creeped in, and we didn’t even discuss it before I’d grabbed the lube and started sliding in a finger or two. He loves it.”

Charlie is staring at Cas with open mouth, and somehow that sets Cas off again.

“Damn, I never thought Dean would be taking it up the ass,” Charlie says through Cas’s laughter.

“Your face…” Cas manages, only barely, “your face is worth gold.”

“I would guess so, yeah.” Charlie sits upright suddenly and stares at Cas. “Should we just ask him together whether he wants a cock up his ass? I think he does, you know.”

“How would you know?” Cas asks. She’s almost afraid to ask, scared that it has something to do with before she transitioned and became much more comfortable in her skin. It’s not the most pleasant part of her life, although it also wasn’t as bad as it could have been.

Charlie takes her hand and squeezes it, quietly reassuring her. “It was before, but God, I don’t know how you never spotted him looking at your crotch area. He was curious even before you said you were trans, so it’s not related to… that. I think.” Charlie scrunches her nose and looks at Cas. “I’m too drunk to properly explain. I think he liked you – maybe even loved you – before you transitioned, but he only fell in love with you once you were comfortable in your skin.”

“But he used to look at my cock?” Cas asks, voice higher than it usually is. Charlie looks at her in concern. Cas isn’t sure whether she wants to cling to Charlie or maybe run to Dean with this revelation. “Interesting.”

Charlie simply blinks and gets up to grab more beer. “I didn’t think that would be your reaction, but I’m glad it is.”

“Well, it _is _interesting,” Castiel says, getting off the couch and following Charlie into the kitchen. “Because I told you I did like this weird thing before surgery, right?”

Charlie nods and it seems like she suddenly understands. Her mouth falls open and she almost drops the bottles of beer she just fished from the fridge. “You didn’t.”

Castiel smiles widely. “I did.”

“Fuck no.”

“Fuck yes.”

“Did you… how?”

“There’s this kit you can order online, and you make a cast of your cock, which is uncomfortable as fuck, and then you send the cast back to the manufacturer with like… the specifications. Hard or soft, the material you want, the colour…” Castiel chuckles, taking one of the beers from Charlie and opening it quickly. “It got delivered a few weeks after my surgery, but I figured it would be weird to use it myself. You know, fucking yourself back on your own cock is just… strange and narcissistic, I figured. So yeah, it’s not been used, still in the original package.”

Charlie shakes her head, smiling. “Dean hasn’t found it yet?”

“Nope,” Cas says. She fills a glass with water, too, resolving that this is going to be her last beer.

“Maybe you should at least try to… put it in a place where Dean can find it?”  
“He won’t know that it’s a copy of my own cock,” Castiel says. “And I think that it might require… some more work before he allows me to peg him with it.” She sighs wistfully. “Although it’s something nice to look forward. I’d almost forgotten about the dildo.”

“We’ll invite him for our next girls’ night out, get him drunk on whiskey, and then ask him all about his preferences,” Charlie promises.

“I don’t know if I can wait very long,” Cas confesses. “I’ve been drooling over his ass since I got to know him and just thought I was gay and confused about what gender was.”

“Why didn’t you ever tell me that?” Charlie says. She sounds like she’s accusing her of a heinous crime, but Cas knows better. “I thought I knew all about your crushes!”

“I did mention I was falling for Dean, didn’t I?”

“Yeah, you did, but that was after that awful surgery when you were high on _fucking drugs_.”

Castiel shrugs. “I told you, and that should count for something. And now you know that this was going on for way longer than you thought it was. You’re the first person who knows this. You’re the first person who knows that I want to peg Dean with a dildo created to be an exact replica of my own fucking cock.”

Charlie deflates. “Okay, yeah, I’ll take that. So are we planning the next girls’ night or what? In a few days?”

“I’ll text you when I’m near my planner – because Dean needs to be here, too. We can’t just leave him out like this and I’m looking forward to seeing my boyfriend drunk and spilling his secrets.”

“You’re staying over, right?” Charlie asks, concerned now that their conversation seems to be winding down. She knows Cas cannot hold her liquor as well anymore, but they usually figure this bit out _before _they get too drunk to do anything.

“Yeah,” Cas says, already snuggling into Charlie on the couch. “Texted Dean a while back that I was staying at your place. He just replied with a heart so it should be okay.”

Charlie looks down at the snuggling monster on her lap, and sighs. “We are going to move to the bedroom, okay? I don’t want to sleep on the couch tonight. _And _we’re both drinking at least one glass of water. I don’t care if you brush your teeth or not, but I don’t want you dehydrated in the morning.”

“Okay, mom,” Cas says, slowly sitting upright again. “I’ll go drink that glass of water now and crash on your bed, okay?”

“Okay,” Charlie says. “I’ll follow in a bit, just going to go clean up some of the beer bottles.”

Cas nods and leaves the room slowly but steadily. Charlie almost laughs at her unsure gait, but doesn’t, because she knows her own is just as bad. By the time she’s done and has drank her own glass of water and brushed her own teeth, Cas is fast asleep in her bed. If Cas and Dean weren’t such a great couple, Charlie would claim Cas as her own – Cas was too precious for the world. With that thought, she slid under the covers and fell asleep almost immediately.

**Author's Note:**

> Please let me know what you think - I'm open to criticism (be kind though). This was my first time ever writing a trans character, and two lovely people looked it over for me, but I would love to know what you think.  
If you want to contact me privately, you can find me on tumblr and pillowfort as fpwoper.


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